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660 Penfield Rd, Fairfield
$10,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212473 MLS
Steps to miles of sandy beaches, breath taking water views, newly remodeled to perfection, and set on an oversized and level .41 acre lot - 660 Penfield Road is a coastal haven! This spacious 8 room, 4 bedroom, 3 full bath rental has features that make it a stand-out; new hardwood white oak flooring throughout, custom shiplap millwork, 2 fireplaces, multiple decks with water views, an open floor plan, new eat-in kitchen, updated baths, freshly painted interior and exterior, 2 car garage, storage, and the list goes on. This designer home is flooded with natural sunlight in every room. Extend your entertaining to the outdoors in your expansive, private and park-like yard - ideal for entertaining. Enjoy your outdoor shower after swimming at the beach. You get the best of both worlds in this prime Beach location as you can walk to great destinations; the beach and enjoy all of the beach festivities, school, playgrounds, and train OR bike to town and enjoy the theatre, shopping, and amazing restaurants. 660 Penfield Road shows and feels like a vacation resort all year long. This gorgeous rental is a special and rare beach area find.

660 Penfield Rd, Fairfield
43-45 Helen St, Fairfield
$1,299,000
7 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217125 MLS
An exceptionally rare opportunity in the heart of Fairfield! Completely rebuilt from the ground up, this stunning new two-family home offers the perfect combination of coastal sophistication, modern efficiency, and exceptional investment potential. Tucked into one of Fairfield's few "hidden gem" neighborhoods, the location is everything: steps from Post Road's shopping, dining, and entertainment, with the train station, Fairfield University, and beautiful beaches all within easy reach. Whether you're an owner-occupant seeking supporting rental income, a savvy university investor, or looking to build long-term wealth in one of Fairfield County's most desirable communities, this turnkey property checks every box. Meticulously crafted with low-maintenance shingle-style siding, composite decking, natural white oak hardwood floors, modern shaker cabinetry, quartz countertops, coastal-inspired bathrooms, and recessed lighting throughout. High-efficiency systems include natural gas heat, central air, on-demand hot water, and separate in-unit laundry. Beautiful new landscaping, classic white picket fencing, abundant off-street parking, and sun-filled interiors complete the picture. The first unit features 3 bedrooms, 1 full bath, an eat-in kitchen, living room, and private rear deck. The spacious upper residence spans the second and third floors, with 4 bedrooms, 2 full baths, an eat-in kitchen, living room, and versatile flex space. THE WORK IS DONE! All that's left is opportunity.

43-45 Helen St, Fairfield
54 Steep Hill Rd, Fairfield
$599,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217015 MLS
Amazing potential is found at this expanded Ranch style home that had an extensive renovation and addition in 2001. Located on a quiet cul-de-sac in Southport. Unbelievable space and floor plan shows the quality details found - expressing the love this home had at one time. Home is occupied and will be sold in "as is" condition. Subject to probate approval. Home will not qualify for conventional financing due to disrepair. Cash or rehabilitation loan only. Do not walk property as it is occupied - listing agent will accompany all limited showings.

54 Steep Hill Rd, Fairfield
1012 Reef Rd, Fairfield
$799,900
2 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24216112 MLS
Location, Location, Location! Enjoy the very best of Fairfield from this lovingly maintained 2-bedroom, 1.5-bath Ranch offering 1,562 square feet of comfortable living space and a detached 1-car garage, all just a short stroll to the beach. Ideally situated near the heart of Fairfield, this wonderful home offers the ultimate in convenience and coastal charm! Enjoy the fabulous restaurants and shops in downtown Fairfield, or hop on the train. Lovingly cared for over the years, the home was raised in 2000 and features natural gas heat and central air conditioning. Whether you're looking to downsize or expand this is a fantastic opportunity!

1012 Reef Rd, Fairfield
601 S Pine Creek Rd Unit 601, Fairfield
$5,300
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215888 MLS
FABULOUS Walk-to-Town Living on South Pine Creek! Enjoy the best of Fairfield living from this inviting townhouse, located mins from South Pine Creek Beach, train, town, restaurants, golf, tennis, and so much more! Sought-after open floor plan offers the perfect blend of comfort & space. Spacious kitchen flows seamlessly into the dining and family rooms, creating a bright, welcoming gathering space with two sets of sliding glass doors that flood the interior with sunshine and open onto a large deck-perfect for outdoor dining & relaxing. Enjoy your own private, fenced yard with plenty of room to play. Upstairs, retreat to the spacious primary suite featuring a generous en-suite bath and walk-in closet. 2 additional well-sized bedrooms on this level w/ one offering its own walk-in closet. Conveniently located laundry room adds everyday ease, while an impressive bonus dressing room/oversized hall closet offers exciting possibilities for a dedicated home office or additional storage. A bright, double-entry foyer welcomes you home, while an attached garage and private driveway with parking for 2 additional cars provide added convenience. An exceptional opportunity to enjoy the Fairfield lifestyle! Walk to the beach, tennis bubble, golf, restaurants, train, and downtown Fairfield-all from this fabulous South Pine Creek location. Don't miss the chance to make this wonderful townhouse your next home!

601 S Pine Creek Rd Unit 601, Fairfield
98 Banks Pl, Fairfield
$5,995,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24216271 MLS
Timeless luxury meets exceptional craftsmanship at 98 Banks Place, where a meticulous restoration & rebuild, completed in 2017, transformed an 1830 Greek Revival into a home offering the comfort of new construction while preserving the soul, warmth, & character only a home of this era can provide. Original floors, brick, timbers, custom windows, reclaimed hardware, & period details blend seamlessly with custom millwork, barrel ceilings, Belgian stone flooring, designer finishes, radiant-heated floors, & all-new systems. A chef's kitchen w/ concealed scullery anchors gracious living spaces, while an inviting family room & serene primary suite balance gathering & retreat. Set on nearly 5.5 private acres, the property is designed for indoor-outdoor living w/ a resort-style pool, year-round spa, expansive bluestone patio, outdoor kitchen, double-sided fireplace, & new pool house offering flexible space for guests, entertaining, an in-law suite, or future living accommodations. Sweeping lawns, formal gardens, an apple orchard, enclosed vegetable garden, & mature green screening create a private retreat unlike any other. Moments from Southport Village, Southport Harbor, Pequot Library, Southport Beach, dining, & the train, this is a rare opportunity to enjoy estate-like living in one of Fairfield County's most sought-after coastal communities, where old-world charm, modern ease, & a walkable coastal lifestyle come together in a truly one-of-a-kind offering.

98 Banks Pl, Fairfield
148 Southport Woods Dr Unit 148, Fairfield
$575,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24215215 MLS ⋅ Southport Woods BLDG.
Live the Southport lifestyle at Southport Woods, where coastal charm meets resort-style living! This beautiful, freshly painted 2-bedroom, 2-bath first-floor condo new A/C offers the ease of single-level living in a sought-after community conveniently located near everything Fairfield, Southport, and Westport have to offer. The spacious, light-filled layout creates a warm and welcoming atmosphere, while the large, covered patio provides the perfect spot to enjoy your morning coffee, unwind in the evening, or entertain friends. Enjoy a carefree lifestyle with wonderful community amenities, including a heated swimming pool, clubhouse, and paddle tennis courts. Ideally situated just minutes from Southport Village, Southport Harbor, beautiful beaches, fine dining, shopping, and Metro-North, this move-in-ready home offers the perfect blend of comfort, convenience, and lifestyle. Whether you are looking to simplify your living, enjoy a relaxing retreat, or embrace all that coastal Fairfield County has to offer, Southport Woods is a wonderful place to call home!

148 Southport Woods Dr Unit 148, Fairfield
70 Southfield Rd, Fairfield
$1,375,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215701 MLS
Wonderful opportunity to live in the sought-after South Pine Creek neighborhood. Beautiful and ideally situated on sought-after street BETWEEN TOWN & BEACH. 2022 complete renovation of 1st floor and part of 2nd floor. New Kitchen, powder room, 2nd floor bath, hard wood floors, electric, plumbing and mechanicals, freshly painted interior and more. Shows like new! Beautiful new open plan kitchen with quartz counters, stainless-steel appliances & pantry. Kitchen flows to inviting family room with a wall of windows and glass door leading to expansive deck overlooking fully fenced yard. Family room flows to sunny dining room with built-ins and living room with fireplace. Primary bedroom expansion with custom closets and ensuite primary bath featuring air jet tub, glass shower, dual sinks & private WC. 2 additional oversized bedrooms with large custom closets complete the 2nd floor. Laundry room & large cedar closet in lower level complete this fantastic home. Easy walk to train & vibrant Fairfield town center. Just a mile stroll to Pine Creek beach, golf and tennis. Seven minutes to scenic Southport village & harbor. No flood insurance required. Waterfront community 50 miles from NYC offering coastal charm, historic character, wonderful dining, shopping & arts. Don't miss this opportunity to live the easy in-town/beach lifestyle!

70 Southfield Rd, Fairfield
448 Pequot Ave, Fairfield
$1,799,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24213940 MLS
Historic 1834 farmhouse located in the heart of Southport Village. From the moment you walk through the door you will feel like you are home. Thoughtful renovation of its iconic Pequot Avenue location in 2016 earned the Southport Conservancy Recognition for Restoration. The foundation was completely rebuilt and the home was elevated to FEMA height regulations. All new plumbing and electrical systems were installed. The original wide plank floors, brick and beams were restored to create an inviting open concept. Professionally designed gardens provide beauty and privacy in the outdoor spaces. A rare opportunity to be just steps away from charming Village shops, Southport Harbor and Metro North. This home offers everything from beauty, convenience and warmth. Welcome Home. Listing agent is related to seller.

448 Pequot Ave, Fairfield
78 Unquowa Pl Unit 306, Fairfield
$3,500
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215342 MLS
Step into Unit #306 at the Fairfield Station Lofts, the premier Metro-North commuter location in Fairfield County, where sleek city sophistication seamlessly fuses with timeless Connecticut charm. Designed by the award-winning Granoff Architects, this boutique project redefines modern living with bold urban design, meticulous craftsmanship, and an unparalleled sense of style. This stunning, 835 sq ft, 1-bedroom, 1-bathroom third-floor loft features soaring 9+ foot ceilings and oversized black-framed windows, flooding the space with natural light and framing picturesque views. Crisp white interiors and rich wood-grain floors (LVT) provide a clean, timeless canvas, perfectly complemented by best-in-class finishes throughout. The heart of the home is a chef-inspired kitchen with stainless steel appliances, a generous center island, and an open flow into the living and dining areas-ideal for entertaining or relaxing in style. Thoughtful amenities include an in-unit stacked washer and dryer, abundant multi-purpose storage, and expansive closets. Step outside to the gorgeous rooftop terrace, a shared oasis with sweeping views, available for private use twice a year. Modern conveniences elevate daily living: 6 EV charging stations, 24/7 Carson remote doorman service, and a one-car garage parking space for ultimate downtown convenience. The Fairfield Station Lofts isn't just an apartment, it's a statement, offering a true introduction to the elevated lifestyle of Fairfield County!!

78 Unquowa Pl Unit 306, Fairfield
78 Unquowa Pl Unit 304, Fairfield
$3,500
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215334 MLS
Step into Unit #304 at the Fairfield Station Lofts, the premier Metro-North commuter location in Fairfield County, where sleek city sophistication seamlessly fuses with timeless Connecticut charm. Designed by the award-winning Granoff Architects, this boutique project redefines modern living with bold urban design, meticulous craftsmanship, and an unparalleled sense of style. This stunning, 835 sq ft, 1-bedroom, 1-bathroom third-floor loft features soaring 9+ foot ceilings and oversized black-framed windows, flooding the space with natural light and framing picturesque views. Crisp white interiors and rich wood-grain floors (LVT) provide a clean, timeless canvas, perfectly complemented by best-in-class finishes throughout. The heart of the home is a chef-inspired kitchen with stainless steel appliances, a generous center island, and an open flow into the living and dining areas-ideal for entertaining or relaxing in style. Thoughtful amenities include an in-unit stacked washer and dryer, abundant multi-purpose storage, and expansive closets. Step outside to the gorgeous rooftop terrace, a shared oasis with sweeping views, available for private use twice a year. Modern conveniences elevate daily living: 6 EV charging stations, 24/7 Carson remote doorman service, and a one-car garage parking space for ultimate downtown convenience. The Fairfield Station Lofts isn't just an apartment, it's a statement, offering a true introduction to the elevated lifestyle of Fairfield County!!

78 Unquowa Pl Unit 304, Fairfield
140 Labbance Ln, Fairfield
$1,695,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199251 MLS
Cross a babbling brook to a European styled Greenfield Hill home set in magical 2 manicured acres. Charming home showing attention to detail. 3 Fpls, Blt-Ins, Scrn Porch, Crown Molding. Expansion for 4th bedroom possible

140 Labbance Ln, Fairfield
1170 Fairfield Beach Rd, Fairfield
$15,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24213139 MLS
Experience coastal living at 1170 Fairfield Beach Road. This beautifully furnished new construction home with deeded beach access is available for a short-term rental through May 31, 2027. The open main level brings together a stylish kitchen, living room and dining area, with a walk-in pantry for added convenience. The second floor features the primary bedroom and two additional bedrooms, while the third-floor bonus room offers flexible space for a family room or fourth bedroom. Take in panoramic water views from the rooftop deck, enjoy long walks along the beach and settle into the relaxed pace of life by the shore. Just 50 miles from New York City, Fairfield offers coastal charm, historic character, wonderful restaurants, shopping and a vibrant arts scene. A welcoming retreat to enjoy beach living beyond the summer season.

1170 Fairfield Beach Rd, Fairfield
96 Clinton St, Fairfield
$15,500
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24209570 MLS
AMAZING RENTAL OPPORTUNITY! BRAND NEW CONSTRUCTION! Never lived in before! This PRIME location is a quick walk to miles of Beaches, Sherman Elementary, Sandcastle Playground, South Benson Marina, shops, restaurants and everything that the sought-after Town of Fairfield has to offer. This beautiful home features four bedrooms, three-and-a-half baths and high-end finishes throughout. The open-concept main level is ideal for everyday living and entertaining, with a chef's eat-in kitchen featuring a large island with two-inch-thick Quartzite countertop, and custom cabinetry. The kitchen flows easily into the spacious dining area and family room, where oak-beamed ceilings, a stone gas fireplace, built-ins and a welcoming bar area create the perfect place to gather. Upstairs, the second level has three generously sized bedrooms, including the primary en-suite with a private bath and walk in closet. The third level offers the fourth bedroom or home office, a full bath and access to a spectacular deck with wire railings and beautiful views-a perfect spot to work or relax. The finished lower-level loggia provides even more living space, complete with custom built-ins, a large-screen TV hookup, and direct access to the patio and backyard. A large mudroom and two-car garage and outside shower add everyday convenience to this special home. With great living space, stunning finishes and an amazing walk-to-everything location, 96 Clinton offers the best of Fairfield Beach living!

96 Clinton St, Fairfield
541 Sasco Hill Rd, Fairfield
$6,500,000
5 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24213955 MLS
Prestigious location. Stately presence. Exceptional living. Introducing a premier 1.25-acre Sasco Hill estate offering extraordinary luxury across 4 levels. This magnificent residence features 5 bedrooms, 9 baths & an uncompromising attention to detail. Outdoors, a private resort awaits with a heated pool & spa, fully equipped outdoor kitchen & expansive terrace overlooking exquisite gardens. An accessory apartment above the garage offers future potential, with plumbing & electrical rough-ins in place. Iron gates flanked by stone lions welcome you to a grand 2-story foyer. The main level showcases exceptional craftsmanship, from the stately living room & Gatsby-inspired formal dining room with garden views to the impressive chef's eat-in kitchen, spacious billiards room, inviting family room & private 1st-floor office. Elegant millwork enhances every room. The 2nd level features 4 luxurious en-suite bedrooms, including 2 primary suites with impressive walk-in closets & dressing rooms. The 3rd level offers flexible living space, including a home gym, bonus room with cedar closet & 5th en-suite bedroom. The finished lower level is an entertainer's dream, complete with an 8-seat home theater, recreation room & storage. Notable upgrades include a new wood roof, Belgian stone & oil-chip driveway, front gates, fencing, updated central air, whole-house generator & finished lower level. Discover extraordinary estate living in Fairfield's prestigious Sasco Hill neighborhood.

541 Sasco Hill Rd, Fairfield
126 Dwight St, Fairfield
$1,225,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24209843 MLS
A lifestyle so good, you will have to pinch yourself. Ideally situated at the end of a quiet cul-de-sac in the heart of Fairfield, this oversized .37-acre property offers a rare combination of in-town convenience, privacy & potential. Just minutes from downtown, shopping, beaches, golf, dining & train, you can enjoy effortless access to everything that makes Fairfield such a sought-after place to call home. This center hall Colonial offers a versatile floor plan with endless possibilities to personalize, expand & create your own space. The main level features hardwood floors, abundant windows filling the home with natural light, a first-floor bedroom & full bath, formal living & dining rooms, a kitchen & an amazing great room with cathedral ceilings overlooking the beautifully landscaped, fenced grounds with INGROUND POOL. Upstairs, 3 generously sized bedrooms & 2 full baths provide a comfortable living space with great flow. Additionally, the pull-down attic presents possibility for future expansion, including additional finished space or an area to create a new primary suite. The full, dry basement offers even more flexibility for future finished space & storage. Once outdoors, the fully fenced backyard is a private retreat, with professional landscaping framing the in-ground pool & plenty of additional front & side yard space to enjoy. Owner has plans for primary suite addition on 2nd floor over the existing Great Room. A perfect location walkable to town and beach.

126 Dwight St, Fairfield
301 Spruce St, Fairfield
$3,400
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24213289 MLS
Enjoy comfortable living in the desirable coastal community of Southport, Connecticut! This inviting 2-bedroom, 2-bathroom half duplex offers a wonderful combination of convenience, comfort, and privacy in a sought-after Fairfield County location. The home features a functional layout, central air conditioning, and the convenience of main-floor laundry. Outside, enjoy a shared private yard, perfect for relaxing and enjoying the outdoors. A private driveway with two dedicated parking spaces adds to the ease of everyday living. Ideally situated near Southport Village, local shops, restaurants, beaches, parks, and the train station, this rental offers convenient access to transportation and everything the surrounding area has to offer. Whether you're commuting, downsizing, or looking to enjoy the charm of coastal Connecticut, this property is a wonderful place to call home.

301 Spruce St, Fairfield
280 Brookbend Rd, Fairfield
$1,549,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24212214 MLS
AN EXTRAORDINARY HOME. AN EXCEPTIONAL LIVING EXPERIENCE IN WINTON PARK. Welcome to one of the most exciting homes to hit the market! Rarely does a home offer such an experience at every turn. From the moment you enter, you are greeted by soaring ceilings, dramatic architectural details, and incredible expanses of glass letting the outside in. This is a home where nature becomes part of your everyday living. Beautifully maintained and thoughtfully updated, this remarkable residence has a fabulously designed kitchen - one you'd love spending time in. An inviting dining room highlighted by a stunning exposed brick accent wall, sets the stage for memorable gatherings and a dining experience that is anything but ordinary. And everyone loves a sunroom! Two separate living spaces each with a stunning architecturally designed fireplace, four generously sized bedrooms including a beautiful en suite primary retreat. And then there is the yard - truly magical! Set on nearly an acre of lush, rolling and level grounds, with a collection of charming outdoor vignettes creates distinct spaces for entertaining, relaxing and gathering with friends. The custom-enclosed garden with water source is a gardeners dream. Every turn there is something to discover, something to appreciate. This is not simply a home to see, it is a home to experience and an experience you won't soon forget.

280 Brookbend Rd, Fairfield
67 Craig Ct, Fairfield
$2,300,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24213049 MLS
Welcome to the Fairfield Beach lifestyle, where spectacular sunrises, coastal breezes and days by the water are part of everyday living. Just steps from the beach, this inviting coastal home offers four levels of spacious living, with views of Long Island Sound from three levels. Enjoy morning coffee or leisurely lunches on the covered porch overlooking the water, or spend evenings in the private, fenced backyard with expanded stone patio and low-maintenance landscaping. The main level features an open kitchen with chef-grade appliances, spacious dining area and inviting living room with fireplace and French doors to the porch. The second level offers an expansive primary suite with fireplace, walk-in closet, private deck overlooking the Sound and spa-like bath with soaking tub and separate shower, plus a second ensuite bedroom. The third level features two additional bedrooms and a full bath. A versatile garage space with glass overhead door expands possibilities for entertaining, recreation or fitness. Recent improvements include interior and exterior painting, refinished wood floors and updated lighting. Enjoy nearby South Benson Marina, beachside recreation and easy access to downtown Fairfield's shops, restaurants, Metro-North and more.

67 Craig Ct, Fairfield
72 Old Barn Rd, Fairfield
$2,399,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24212223 MLS
Winton Park is the type of address that people in Fairfield already know by name. Incorporated by special act in 1937, it is a private association spanning an est. 70 acres on just a few tree-lined streets w/stone pillars at the entrances, one-acre zoning, mature plantings, & the quiet authority of an established, walkable neighborhood. People call it "downtown's Greenfield Hill" for a reason. You get the soft structure & privacy of the Hill, & you are still inside the life of town. Introducing 72 Old Barn Road. This classic colonial has front & back staircases, a covered front entry, wood-burning fireplace, a screened porch & a private backyard w patio & built-in firepit. Hardwood floors run through the house, with charming design details & generous closets throughout.The large front-to-back chef's kitchen has top-of-the-line appliances and a large center island that seats six. Upstairs are 4/5 bedrooms & 3 full baths, including an oversized primary suite w/ a vaulted ceiling & large, walk-in closet. Beside it, a private second-floor office w/custom built-ins overlooks the backyard. A finished lower level offers room for a playroom & gym, den or game room. Winton Park is a neighborhood that cannot be replicated. Downtown Fairfield, shops, restaurants, theaters & Main Library, & Fairfield University are all right there. Ludlowe Middle School, Fairfield Ludlowe High School & the Metro North Station are a short walk or an easy bike ride away, along quiet side roads.

72 Old Barn Rd, Fairfield
1180 Oldfield Rd, Fairfield
$5,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24212976 MLS
Enjoy the best of Fairfield living in this beautifully appointed, newly built one-bedroom apartment in the sought-after Sasco neighborhood. Thoughtfully designed with quality finishes and attention to detail throughout, this charming residence features a beautiful kitchen with stainless steel appliances, custom cabinetry and stone countertops, a comfortable living area, spacious bedroom and stylish full bath. Additional highlights include hardwood floors, recessed lighting and the convenience of an in-unit washer and dryer. Enjoy the privacy of your own separate entrance, driveway and outdoor patio. All utilities, internet, trash removal and grounds maintenance, are included in the rent, offering easy, maintenance-free living. Ideally located within walking distance to Sasco Beach, downtown Fairfield, restaurants, shopping and the train. A wonderful opportunity to enjoy coastal living in one of Fairfield's most desirable neighborhoods, with the perfect combination of charm, comfort and convenience!

1180 Oldfield Rd, Fairfield
590 Sturges Hwy, Fairfield
$5,975,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24209002 MLS
For those who believe luxury should never feel predictable. This remarkable Southport estate is a masterful reinvention of new construction...where timeless architecture meets modern artistry, extraordinary craftsmanship, and effortless living. Every element feels intentional, from dramatic windows and beautifully scaled rooms to custom millwork, sophisticated lighting, advanced technology, and finishes chosen for beauty rather than trend. Walls of glass dissolve the boundary between indoors and out, revealing a private, beautifully landscaped setting with a breathtaking pool and cabana...a sanctuary that feels worlds away, yet is moments from everything. 8800 Sqft of unsurpassed quality offering an exceptional floor plan that must be experienced to be appreciated. Chef's will appreciate the exceptional Kitchen, the primary suite is an indulgent retreat, while exceptional entertaining spaces make the home equally suited to intimate evenings and unforgettable gatherings. A completely separate, perfectly renovated guest house with its own address, utilities & garage offers a rare luxury in itself...privacy & possibilities for guests, extended family, office, caretaker or rental income. And the location may be the ultimate luxury: the beauty and charm of Southport, award-winning Fairfield schools, beaches and amenities, and coveted Westport resident privileges including Compo Beach and Longshore. One extraordinary property. Two exceptional lifestyles. In a word...Perfection.

590 Sturges Hwy, Fairfield
190 Beaumont St, Fairfield
$6,500
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24212181 MLS
Welcome to 190 Beaumont St., a spacious and beautifully maintained half-duplex offering the feel and privacy of a single-family home in an ideal Fairfield location. Just minutes from downtown, restaurants, shopping, and the train station, this home offers generous living space and plenty of room to spread out. The main level features a bright living room with marble fireplace, hardwood floors, crown molding, and recessed and sconce lighting, along with a formal dining room with chair rail and double doors. The eat-in kitchen features custom cabinetry, granite countertops, stainless steel appliances, and direct access to a private deck and fenced backyard-perfect for entertaining or relaxing outdoors. Upstairs, the spacious primary suite offers a private full bath, large walk-in closet, and sitting area, while two additional bedrooms provide generous space and storage. The finished lower level adds valuable flexible living space ideal for a family room, home office, gym, or playroom. With its private yard, generous layout, and convenient location, this is a fantastic Fairfield rental.

190 Beaumont St, Fairfield
245 Unquowa Rd Unit 44, Fairfield
$599,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211695 MLS ⋅ Mosswood BLDG.
Welcome to Mosswood condominiums: A must see updated second floor residence in this Fairfield sought-after well maintained complex. Perfectly located within walking distance to train, shopping and area restaurants. Interior was just repainted. Beautifully updated, renovated kitchen and two full bathrooms. New window treatments and lighting. Impeccably maintained. Large rear deck overlooking courtyard. Reserved parking space #65. visitor parking is first come/first serve. Real estate agent is related to the seller.

245 Unquowa Rd Unit 44, Fairfield
245 Unquowa Rd Unit 42, Fairfield
$2,800
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211070 MLS ⋅ Mosswood BLDG.
Privately located in the interior courtyard of the desirable Mosswood Condominiums, this second floor 2-bedroom 2 bath unit has been updated and freshly painted! A short walk to the common parking area with one assigned parking space #54 and visitor parking. Just a few minute walk to the train station-no parking fees and ideally situated to downtown Fairfield with its shops, restaurants, beaches and schools. Enjoy the remodeled kitchen with quartz counter tops, stainless steel appliances, subway tile backsplash which compliments the white kitchen cabinetry. Spacious sun-filled living room with hardwood floors and dining area with access to the private balcony/deck. Grills are not permitted in the complex. Spacious Primary Bedroom with its own full bath and walk-in closet plus an additional closet. The 2nd bedroom is also generous in size, and both bedrooms have hardwood floors. The second bathroom is equipped with tub and shower. Tenants are permitted 2 cars which includes one reserved parking space #54 and use of visitor parking for the second vehicle. Additional basement storage is included, and the owner takes no responsibility for usage! A commercial coin-operated laundry facility is available in the same building. The owner will NOT consider pets or smokers with no exceptions! Rent spree application for all interested tenants. Available immediately to enjoy everything Mosswood and Fairfield have to offer!

245 Unquowa Rd Unit 42, Fairfield
97 Gorham Rd, Fairfield
$1,049,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24205924 MLS
Step into this charming expanded Cape, ideally located on a quiet cul-de-sac in the heart of the coveted South Pine Creek beach area. Filled with warmth and character, this inviting four-bedroom, two-bath home is move-in ready while offering wonderful potential to expand in the future. Set on a flat .22-acre parcel, the property provides a fantastic opportunity in one of Fairfield's most desirable coastal neighborhoods. Inside, an open living and dining space creates an easy, comfortable flow, with sliders offering views and direct access to the backyard. The bright white kitchen features an eat-in area and convenient mudroom space. A first-floor bedroom and full bath provide flexibility for guests, a home office, or main-level living. Upstairs, the spacious primary bedroom offers generous closet space and is joined by two additional bedrooms and a beautifully renovated full bath. The finished lower level provides additional flexible living space, ideal for a playroom, home office, gym, media room, or bonus room. Enjoy the best of the Fairfield beach lifestyle with the beach, town, restaurants, shops, and train all within easy reach. A charming, happy home in a truly fantastic location!

97 Gorham Rd, Fairfield
11 Oldfield Dr, Fairfield
$1,150,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209127 MLS
11 Oldfield Drive offers the rare combination of neighborhood charm, a turnkey home, and an exceptional in-town location. Set on a quiet cul-de-sac, this classic Cape features approximately 2,000 square feet of finished living space with four true bedrooms, two full baths, and a finished lower level offering valuable flexibility for a home office, playroom, gym, or additional living space. The bright white kitchen is equipped with Viking appliances and opens to the inviting living room, anchored by a wood-burning fireplace. Outside, the fenced yard is designed for easy everyday living and entertaining, with a dining patio, mature arborvitaes providing privacy, and a classic white picket fence framing the front of the property. Best of all is the location: tucked away on a peaceful street while still within an easy walk of town, the train, and beaches. Move-in ready and ideally situated, 11 Oldfield Drive is a wonderful opportunity to enjoy the best of Fairfield living.

11 Oldfield Dr, Fairfield
1859 Fairfield Beach Rd, Fairfield
$6,499,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24207566 MLS
A rare and extraordinary Long Island Sound waterfront estate, offering over half an acre and nearly 100 feet of direct beach frontage across two parcels (1845 & 1859 Ffld Bch Rd). Set along one of Fairfield's most coveted stretches of shoreline, this exceptional property presents a unique opportunity to create a private coastal compound with an abundance of space, water access, and privacy. The expansive 0.55-acre property features a gracious main residence with an airy second floor offering three bedrooms and a bonus room, along with an additional 748 sq ft on the third floor, creating the potential for sweeping Long Island Sound views. The main residence is complemented by a private in-ground pool and a separate two-car garage. Across the property, a creekside boathouse offers an extraordinary additional dimension, featuring a finished studio apartment, a second two-car garage, and a private dock with creek access. A beautifully manicured, fenced-in grassy lot provides an exceptional sense of privacy and offers generous space for outdoor entertaining, recreation, or exploring future possibilities. With its combination of expansive grounds, direct beach frontage, private dock, pool, two separate two-car garages, and versatile additional living space, this is an exceptionally rare waterfront offering. Buyer to perform their own due diligence with the Town of Fairfield regarding all building, renovation, zoning, and waterfront development possibilities.

1859 Fairfield Beach Rd, Fairfield
891 Oldfield Rd, Fairfield
$1,395,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24209087 MLS
NEW PRICE. An exceptional opportunity to own this impeccably maintained, beautifully designed home just moments from town and the beach. Better than new. Built in 2018 and enhanced with over $175K in recent custom upgrades, this 3-4 bedroom sophisticated three-story residence offers a level of finish, customization and outdoor living rarely found in new construction. Designer interiors feature elevated materials throughout, including a beautifully appointed chef's kitchen and thoughtful custom details. The third-floor flex space offers exceptional versatility for a home office, gym plus guest space or fourth bedroom, with a full bath and additional storage. Outside, lush professionally designed gardens create a private setting with a generous entertaining patio and custom built gas firepit, all backing to beautiful open marshland and nearby walking trails. Ideally located walk/bike to beach and vibrant town center, this impeccable move right-in home combines the look and quality of new construction with the individuality of a custom-built residence. Part of an intimate two-unit condominium on .25 acres lot. The homes share no walls and are connected only by their garages, giving this residence the privacy and feel of a single-family home. No HOA fees. Owners of the two units only share the cost of master insurance policies and certain maintenance expenses.

891 Oldfield Rd, Fairfield
738 Rowland Rd, Fairfield
$1,675,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24200231 MLS
Barely a block from Fairfield Beach this stylish beach house offers bright, designer-chic living with year-round marsh views. The open main level features hardwood floors, a light-filled living area, and a Nantucket-style kitchen with a quartz island and stainless steel appliances. The adjacent dining room leads through French doors to an expanded Trex deck overlooking the marsh. Upstairs, the primary suite boasts a walk-in closet, serene views, and a renovated ensuite bath, alongside two additional bedrooms, a updated full bath, and dedicated laundry. A lower-level mudroom connects to the attached two-car garage and a carved out office space. Highlights include a firepit, outdoor shower, and key upgrades like a new roof, windows, and deck-all just minutes from downtown Fairfield's dining, shops, and train. Gated Beach access awaits you just steps from the house.

738 Rowland Rd, Fairfield

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